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Acetoxylation of methyl oleate with a resin catalyst

  • Technical
  • Published:
Journal of the American Oil Chemists Society

Abstract

The reaction of methyl oleate with acetic acid in the presence of a reticulated cation exchange resin produces methyl acetoxystearate. Saponification of this compound and subsequent acidification yields hydroxystearic acid. Time, temperature, acetic acid:ester ratio, and resin:ester ratio were examined for their effect on yield of methyl acetoxystearate. A yield of approximately 45% of theory was reached under the best conditions. The cation exchange resin promoted ester inter-change with the formation of oleic acid, acetoxy-stearic acid, and methyl acetate. An estolide polymer was formed, probably by ester inter-change between acetoxylated methyl oleate and oleic acid. Acetoxy esters were separated from unreacted methyl oleate and ester polymers by fractional distillation. Molecular weight and GLC data substantiate the product structure. Several other short-chain carboxylic acids were reacted with methyl oleate but gave lower yields of acyloxylated product than acetic acid.

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Authors and Affiliations

  1. Northern Regional Research Laboratory, Peoria, Illinois

    L. T. Black & R. E. Beal

Authors
  1. L. T. Black
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  2. R. E. Beal
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No. Utiliz. Res. Der. Div., ARS, USDA.

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Black, L.T., Beal, R.E. Acetoxylation of methyl oleate with a resin catalyst. J Am Oil Chem Soc 44, 310–312 (1967). https://doi.org/10.1007/BF02635622

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  • DOI: https://doi.org/10.1007/BF02635622

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